I successfully found the same issue that I have mentioned on answers.microsoft.com.but unfortunately the discussion is closed with no resolution except for a referral to Microsoft support. https://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook-mso_mac-mso_mac2016/authentication-issue-with-outlookoffice-365-on/1de038f2-af8c-48d1-b7a1-1fa213c265d4
I attempted to post the same question but answers.microsoft.com won't allow me to post with any browser. Mac or PC.. Bizarre. So I am posing it here.
Here is a summary of my problem with, hopefully, a complete list of troubleshooting procedures followed (albeit without success).
Outlook 2016 Mac 16.16.2 stopped receiving emails for one staff member's account.
“Authentication issue. Check credentials.”
All other users in the office had no issue. All were using same version of Office and Mac OS
Deleted all keychain entries and preferences. Same error.
On the same Mac we successfully logged in to the same email account via webmail in Safari.
On the same Mac we successfully logged in to the same email using Outlook 2011 which was still installed.
On a PC nearby Outlook for Windows successfully logged in to same email account. As did webmail on PC.
Deleted account from Mac and attempted to add new account from scratch using both email address and Domain/User logon methods. Same error.
Manually entered server addresses instead of auto discover. Same error.
Added a different user's account to the same Mac and authentication was successful. Re-entering problem account results in same error.
Tried to add problem account to Apple Mail. Same error.
Tried to add this account to a different Mac in the office with Outlook 2016. Same error.
Even though the problem appeared to be following the account not the hardware we reformatted another Mac and reinstalled Mac OS and Outlook 2016 from original installer (v 16.14.18). Same error in that version too. Upgraded Mac OS to Mojave from High Sierra as well with no success.
Password was changed as well at one point too despite it working in all other scenarios.
This is a large company and has a separate IT support dept that only handles the PC's and being typically uncooperative "We don't support Macs" refused us assistance even though the issue appears account specific in a most bizarre way. I am responsible for the 15 Macs in the organization and am sort of stuck. One option is try and go direct to Microsoft (human) Chat but I wanted to post the question here first in case there are more than 2 of us out there with this odd issue. Perhaps someone can suggest a configuration change for the user’s account at the server end. Can the IT dept do a config reset for that user without deleting the user account?
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